Search Results (5)

The quality of life of patients affected by Parkinson’s disease is improved by medications containing levodopa and carbidopa, restoring the dopamine concentration in the brain. Accordingly, the affordable quality control of such pharmaceuticals is very important. Here is reported the simple and inexpensive colorimetric quantification of carbidopa in anti-Parkinson drugs by the selective condensation reaction between the hydrazine group from carbidopa and the formyl functional group of selected aldehydes in acidified hydroalcoholic solution. An optical assay was developed by using indole-3-carbaldehyde (I3A) giving a yellow aldazine in EtOH:H₂O 1:1 (λ_max~415 nm) at 70 °C for 4 h, as confirmed by LC-MS analysis. A filter-based plate reader was used for colorimetric data acquisition, providing superior results in terms of analytical performances for I3A, with a sensitivity ~50 L g⁻¹ and LOD ~0.1 mg L⁻¹ in comparison to a previous study based on vanillin, giving, for the same figures of merit values, about 13 L g⁻¹ and 0.2–0.3 mg L⁻¹, respectively. The calibration curves for the standard solution and drugs were almost superimposable, therefore excluding interference from the excipients and additives, with very good reproducibility (_avRSD% 2–4%) within the linear dynamic range (10 mg L⁻¹–50 mg L⁻¹). Full article

A mixture of 2-pyridine carboxaldehyde, 4-formylimidazole (or 2-methyl-4-formylimidazole), and NiCl₂·6H₂O in a molar ratio of 2:2:1 was reacted with two equivalents of hydrazine monohydrate in methanol, followed by the addition of aqueous NH₄PF₆ solution, afforded a Ni^II complex with two unsymmetric azine-based ligands, [Ni(HL^H)₂](PF₆)₂ (1) or [Ni(HL^Me)₂](PF₆)₂ (2), in a high yield, where HL^H denotes 2-pyridylmethylidenehydrazono-(4-imidazolyl)methane and HL^Me is its 2-methyl-4-imidazolyl derivative. The spectroscopic measurements and elemental analysis confirmed the phase purity of the bulk products, and the single-crystal X-ray analysis revealed the molecular and crystal structures of the Ni^II complexes bearing an unsymmetric HL^H or HL^Me azines in a tridentate κ³N, N’, N” coordination mode. The HL^H complex with a methanol solvent, 1·MeOH, crystallizes in the orthorhombic non-centrosymmetric space group P2₁2₁2₁ with Z = 4, affording conglomerate crystals, while the HL^Me complex, 2·H₂O·Et₂O, crystallizes in the monoclinic and centrosymmetric space group P2₁/n with Z = 4. In the crystal of 2·H₂O·Et₂O, there is intermolecular hydrogen-bonding interaction between the imidazole N–H and the neighboring uncoordinated azine-N atom, forming a one-dimensional polymeric structure, but there is no obvious magnetic interaction among the intra- and interchain paramagnetic Ni^II ions. Full article

11H-Indeno[1,2-b]quinoxaline derivatives present an important type of nitrogen-containing heterocyclic compound that are useful intermediate products in organic synthesis and have potential pharmaceutical applications. A new 11H-indeno[1,2-b]quinoxalin-11-one-2-(4-ethylbenzylidene)hydrazone (compound 3) was synthesized. Compound 3 is the first example of an azine derivative based on the 11H-indeno[1,2-b]quinoxaline system. The Z,E-isomerism of compound 3 was investigated by DFT calculations. Bioavailability was evaluated in silico using ADME predictions. According to the ADME results, compound 3 is potentially highly bioavailable and has potential to be used for the treatment of neuroinflammation and ischemia–reperfusion injury. Full article

A new approach to the synthesis of selected quinolinecarbaldehydes with carbonyl groups located at C5 and/or in C7 positions is presented in this paper in conjunction with spectroscopic characterization of the products. The classical Reimer-Tiemann, Vilsmeier-Haack and Duff aldehyde synthesis methods were compared due to their importance. Computational studies were carried out to explain the preferred selectivity of the presented formylation transformations. A carbene insertion reaction based on Reimer-Tiemann methodology is presented for making 7-bromo-8-hydroxyquinoline-5-carbaldehyde. Additionally, Duff and Vilsmeier-Haack reactions were used in the double formylation of quinoline derivatives and their analogues benzo[h]quinolin-10-ol, 8-hydroxy-2-methylquinoline-5,7-dicarbaldehyde, 8-(dimethylamino) quinoline-5,7-dicarbaldehyde and 10-hydroxybenzo[h]quinoline-7,9-dicarbaldehyde. Four Schiff base derivatives of 2,6-diisopropylbenzenamine were prepared from selected quinoline-5-carbaldehydes and quinoline-7-carbaldehyde by an efficient synthesis protocol. Their properties have been characterized by a combination of several techniques: MS, HRMS, GC-MS, FTIR, electronic absorption spectroscopy and multinuclear NMR. The electrochemical properties of 8-hydroxy-quinoline-5-carbaldehyde, 6-(dimethylamino)quinoline-5-carbaldehyde and its methylated derivative were investigated, and a strong correlation between the chemical structure and obtained reduction and oxidation potentials was found. The presence of a methyl group facilitates oxidation. In contrast, the reduction potential of methylated compounds was more negative comparing to non-methylated structure. Calculations of frontier molecular orbitals supported the finding. The structures of 8-hydroxy-2-methylquinoline-5,7-dicarbaldehyde and four Schiff bases were determined by single-crystal X-ray diffraction measurements. Full article

A fluorescence chemosensor, 2-hydroxy-1-naphthaldehyde azine (HNA) was designed and synthesized for sequential detection of Cu²⁺ and biothiols. It was found that HNA can specifically bind to Cu²⁺ with 1:1 stoichiometry, accompanied with a dramatic fluorescence quenching and a remarkable bathochromic-shift of the absorbance peak in HEPES buffer. The generated HNA-Cu²⁺ ensemble displayed a “turn-on” fluorescent response specific for biothiols (Hcy, Cys and GSH) based on the displacement approach, giving a remarkable recovery of fluorescence and UV-Vis spectra. The detection limits of HNA-Cu²⁺ to Hcy, Cys and GSH were estimated to be 1.5 μM, 1.0 μM and 0.8 μM, respectively, suggesting that HNA-Cu²⁺ is sensitive enough for the determination of thiols in biological systems. The biocompatibility of HNA towards A549 human lung carcinoma cell, was evaluated by an MTT assay. The capability of HNA-Cu²⁺ to detect biothiols in live A549 cells was then demonstrated by a microscopy fluorescence imaging assay. Full article